


Sam and Dean Do the Sibling Tag

by Pippiuscattius



Series: SPN Characters Do Various Tags [2]
Category: Supernatural
Genre: Brother Feels, Brothers, Dean is Bad at Feelings, Dean is a Little Shit, Family Feels, Gen, Humor, Implied Castiel/Dean Winchester, Mentions of some Past Episodes, Rated T for Language and some Crude Humor, Sam Winchester is So Done, Sam is Also a Little Shit, Sharing Old Stories, Siblings, Silly, Teasing, The Sibling Tag, Video, Video Cameras, Wincest is mentioned once but ONLY as a joke, Winchester Feels
Language: English
Status: Completed
Published: 2018-06-22
Updated: 2018-06-28
Packaged: 2019-05-26 18:19:33
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 30
Words: 7,672
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15006641
Author URL: https://archiveofourown.org/users/Pippiuscattius/pseuds/Pippiuscattius
Summary: One video camera. Two brothers who routinely save the world and each other. Twenty-nine questions designed for normal, non-apocalypse averting siblings.Bring it on.





	1. Introduction

**Author's Note:**

> Here is another one of those "SPN characters doing a tag together" things I promised. This one is set sometime shortly after "Dean and Castiel do the Best Friend Tag," so it's still happening sometime vaguely in season 11 before Casifer bursts onto the scene and shows off Misha's mad acting skills.
> 
> Also Kevin and Charlie are still alive because screw the heartbreak their deaths brought me I just want them to be happy ;w;
> 
> Here's a link to the list of questions I used: https://thetagquestions.com/sibling-tag-questions/

[Camera screen comes into focus. Dean Winchester is seated at a table in the bunker’s library, his hand hovering over the camera and fiddling with some part of it. He nods in satisfaction after a few seconds and leans back in his chair.]

Dean: Alright, Sammy, it’s all set up!

[Sam Winchester’s heavy footsteps are heard stomping closer and closer. The moose himself walks into the frame and pulls out a neighboring chair to sit beside his brother at the table. He briefly eyes the camera, then his gaze drifts towards Dean.]

Sam: Ooookaaaay, what exactly is this all about, again?

Dean: We’re doing the sibling tag! [Pulls a list of questions up off the table and presents it to Sam]

Sam: The sibling… [Scrutinizes the list in a highly unamused fashion] Is this like some version of that video Charlie made you and Cas do a while back?

Dean: Kinda. That video ended up being more fun than I expected, so I figured, why not do another one? Except much shorter, because the one I did with Cas just went on and on and _on_.

Sam: Yeah, you guys were sitting there answering questions for at least an hour.

Dean: Rest assured that will not be the case this time. We’re doin’ this for forty minutes, tops.

Sam: And another thing: why are you roping me into this?

Dean: Uh, ‘cause it’s the sibling tag? And you’re my sibling? Plus, it’ll be like carrying on a Men of Letters tradition.

Sam: [Raises an eyebrow] Pretty sure “tags” didn’t exist back when the Men of Letters did.

Dean: No, I’m talking about how the Men of Letters made tons of recordings of themselves for their archives. This way, we can contribute our own stuff to their records; just with way better technology than they had. We’ll be carrying on the torch, continuing their history…

Sam: [Lighting up somewhat] That…actually sounds really cool when you put it like that.

Dean: So you’re in?

Sam: Yeah, I…I’m in, sure.

Dean: [Looks excitedly at the camera] You heard it here first, folks! I just convinced my brother to willingly do a tag with me, and I didn’t even have to bring out the bribes!

Sam: [Huffing a laugh] Bribes? What were you going to bribe me with?

Dean: I… [Falters] Didn’t think that far ahead. Probably woulda just used some nerdy crap, or promised to make you salad for a week.

Sam: …And I’m guessing neither of those is on the table anymore?

Dean: Nope. Let’s get started.


	2. Question #1: Who's the youngest/oldest between you?

Dean: [Raises a single hand] Oldest here.

Sam: Yeah, not that he acts like it.

Dean: [Offended] I am totally a responsible older sibling! I’ll have you know, I’m an excellent role model.

Sam: [Resonating pure waves of sarcasm] Yeah, sure. And that time you convinced me to try a sip of beer when I was ten, that was completely responsible.

Dean: I didn’t let you drink the _whole_ thing! It was just a taste!

Sam: And when you set an example by jumping off that shed, truly that was the work of an excellent role model.

Dean: I took you to the ER right after!

Sam: On your bike’s _handlebars_.

Dean: I couldn’t drive yet!

Sam: [Finally relents] Alright, alright, I’m giving you a hard time. Responsible or not, you are really good at being an older brother.

Dean: _Thank_ you, jeez. But you, on the other hand, don’t exactly fit into your role of younger brother. You’ve been tryin’ to show me up ever since the first day you were officially taller than me.

Sam: Aren’t younger siblings supposed to annoy their older siblings?

Dean: …Fair enough. But that doesn’t make it any less…annoying.

[Sam smirks.]


	3. Question #2: What do you like about each other?

Dean: [Reclines in his chair] He does all the research. Saves me the trouble.

Sam: Not _all_ of it. You help out sometimes on the serious cases. But yeah, other than that, I have to do most of the research.

Dean: I ‘preciate it. Gives me more time to do…not nerdy stuff.

Sam: Like marathoning Dr. Sexy M.D.? How is that not nerdy?

Dean: I’ve told you once, I’ve told you a million times: Dr. Sexy is not a fandom, it’s a lifestyle. Totally not a nerd thing.

Sam: [Not believing him for one second] Mm-hmm. Well even if you don’t do your share of the research, you do a good job looking out for me. I can look after myself for the most part, but…it’s still good to know you have an older brother who’s got your back.

Dean: [Actually touched by that] …Well gee, now I feel like I gotta give you a genuine compliment, too. I guess…you really are a damn smart kid.

Sam: “Kid?” Dean, I’m thirty-three.

Dean: Yeah, but I still have seniority, so kid it is.


	4. Question #3: What do you hate about each other?

Sam and Dean: [In perfect sync] He lies to me.

[They both silently stare into space for a few moments and then slowly, awkwardly glance at each other.]

Dean: Uh, yeah…we’ve both had problems with keeping secrets in the past. But we’re working on it!

Sam: [Looks uncertainly at the camera] You wanna…give any examples for the sake of posterity?

Dean: Not really. I don’t want to a have another conversation with the words “demon blood” or “Ezekiel” in it ever again if I can help it.

Sam: Yeah, no argument here…


	5. Question #4: What annoys you most about each other?

Dean: Hair. Just… [Wildly gesture’s at Sam’s moose locks] _Look_ at it! I swear I have to physically restrain myself not to reach for the scissors whenever they’re in the same room as him.

Sam: [Grasps protectively at his hair] Don’t knock long hair ‘til you’ve tried it, Dean!

Dean: Not happening, there is no way in hell I’d grow my hair out. It’s borderline dangerous for a hunter to have long hair! I’m surprised a demon hasn’t strung you up by yours yet. And another thing: after having to drive next to you for years, lemme just say that you are the gassiest driving companion on the freakin’ planet.

Sam: You think I can help that? At least that’s out of my control; when you’re driving, on the other hand-

Dean: Oh boy, here we go.

Sam: Do you have to eat with your mouth half-open and spray greasy food bits all over the place when you sing along to your cassettes? And for god’s sake, Dean, would it kill you to keep your eyes on the road? I know you’re good at driving, but I swear you spend more time looking away from the road than at it.

Dean: It’s not like I’m texting and driving! I haven’t gotten us into an accident yet.

Sam: _Yet._ Exactly. A monster isn’t what’s gonna kill you; it’ll probably be either a car wreck or clogged arteries.

Dean: [Glances at the camera] …If we keep this up, the whole video is just going to be sibling bickering.

Sam: …Yeah this is gonna get out of hand really fast if we don’t stop now.


	6. Question #5: What do you have in common?

Sam: We’re both hunters; that’s a good start.

Dean: We’ve both also doomed _and_ saved the world multiple times. [Clicks his tongue] Put _that_ on our résumés.

Sam: We’ve both been to heaven and hell…and purgatory, actually, I did visit it that one time when I rescued Bobby’s soul.

Dean: There should seriously be passports for the spectral planes. We’d have, like, nearly all the stamps.

Sam: And we were both supposed to be vessels for archangels, but that didn’t exactly pan out.

Dean: We’re both card-carrying members of the “I Survived Death” club. We may as well be the club presidents with how many times that’s happened to us, actually… [Smirks to himself] Or maybe not, since I literally killed Death. Still not over that.

Sam: Aaaaaand we’ve been stuck with each other for roughly over a decade now.

Dean: …Man our lives are weird.

Sam: What else is new?


	7. Question #6: What's your funniest memory together?

Dean: [Already smiling] Oh god, how am I possibly supposed to pick? There was the prank war way back when…oh, and when you were attacked by killer clowns and got covered in glitter! And even if it wasn’t that funny at the time, the whole rabbit’s foot incident is hilarious in hindsight-

Sam: I’m picking up a theme of humor at my expense.

Dean: ‘Cause you’re fun to mess with!

[Sam fires a bitchface in Dean’s direction.]

Dean: C’mon, don’t be like that! You’re my little brother, it’s what I’m supposed to do!

Sam: [A smirk ghosts over his face] Okay then. How about that time with the ghost sickness? When you screamed at a cat and fled in terror from a Pomeranian?

Dean: [Falters] Okay, that’s not fair, I was literally _infected_ -

Sam: Or when you were “abducted by aliens?” Soul or not, that really was funny.

Dean: Empathy, Sam!

Sam: Exactly, _empathy_. Shouldn’t we pick a memory that both of us found funny?

Dean: …Alright, fine. I guess that narrows it down…a bit… [Face brightens] Oh wait, I’ve got it. Any given time we’ve pranked the Ghostfacers. God, they’re annoying, but they’re so fun to mess with.

Sam: Right, they were a common enemy for us to wage pranks against. [Face falls somewhat] I do feel kinda bad about them breaking up, though. That ruined the fun.

Dean: …Way to be a downer, Sammy.

**Notes for the Chapter:**

> I feel like I could have thought of a better funny memory for them but everything that came to mind was at the expense of one if not both of them. Why do the boys gotta prank and mess with each other so much ;w;


	8. Question #7: What do you do for fun?

Sam: See, most siblings go out and toss a ball around, or go on a family vacation or something, but we-

Dean: Kill evil sons of bitches and save the world!

Sam: …Yeah…that. Most of our lives consist of hunting monsters, which is actually more fun than it sounds; sometimes.

Dean: And when we’re not on a case, we’ll have family movie nights. That’s about the most normal thing we do for fun, honestly. [Snaps his fingers] Speaking of which, I swore that I’d get Cas to watch the rest of the original Star Wars trilogy soon. You want in?

Sam: Sure. But if it’s Star Wars, you know Charlie’s also gonna want in, and I bet Kevin will too.

Dean: We’ll get the whole bunker in on it! How’s _that_ for having fun?

Sam: Sure beats washing werewolf guts out of my clothes…


	9. Question #8: Who's in love?

[Dean raises an eyebrow as he reads the question and Sam just smirks to himself.]

Sam: [Looking into the camera with a shit-eating grin] Funny you should ask, actually.

Dean: What? You’ve got the hots for someone and I don’t know about it? No way.

Sam: I didn’t say anything about me.

Dean: [Suddenly apprehensive] …Oh c’mon, dude, I’m not-

Sam: [Loudly clearing his throat to interrupt his brother] Dean here has a massive, painfully obvious crush that he’s been harboring for years now.

Dean: Wh…what are you talking abou-

Sam: You can literally see the waves of pining radiating off of him whenever his crush is around. It’s actually kind of sad. They’d be perfect for each other; if they could just figure out how to talk about their feelings, that is. But no, they’re both emotionally constipated and force me to sit and endure all the tension between them that they refuse to do anything about.

Dean: …No seriously, what are you-

Sam: I’ve had to put up with it for so long now, but unfortunately, I still haven’t figured out how to fully tune it out. The sheer force of the endless staring they share is probably enough to power a small city.

Dean: [Getting positively fed up] …I swear to- _what are you_ -

Sam: One could even say they’re… _Cast_ to be together.

[Sam waits expectantly, watching Dean for any reaction. Dean doesn’t offer anything other than a blank stare of confusion.]

Sam: [Sighing] Nothing? Really?

Dean: Yeah, I…I really have no idea what you’re talking about, Sammy.

Sam: So either you’re so far in denial that you really can’t see what’s right in front of you, or you’re just lying because you’re on camera.

Dean: [Glances at the camera] What? No, no, this is all about being transparent for posterity.

Sam: [Not particularly buying it] Yeah, sure. It’s a real shame either way; you’d make a pretty cute couple, perhaps one would even call it…an angelic pairing.

Dean: …I still got nothing.

Sam: [Shaking his head] I wasn’t even trying to be subtle that time. Whatever, it’s not my job to meddle in your love life.


	10. Question #9: Describe your sibling in just three words.

Dean: [Rubs hands together] Ah, I’ve got this! Let’s see…nerd, bitch, and L’Oréal model.

Sam: That’s four words.

Dean: Four words that suit you to a tee.

Sam: …Alright, fine. In that case, you get…stubborn, jerk, and barhopping-grudge-holding-flirt-with-anything-that-moves-big-brother.

Dean: …That…was way more than three words.

Sam: Way more than three words that can be connected with a hyphen. Grammatically it can technically still be three words.

Dean: …Maybe that Stanford education wasn’t all for nothing after all.


	11. Question #10: What's your family call/family nickname?

Sam: Most people just call us “the Winchesters.”

Dean: Yeah, that’s pretty much the standard. Kinda uncreative, but…at least we’re not the “ _Lose_ chesters!”

Sam: [Stares at him for a few moments] That…was probably one of your worst jokes ever.

Dean: …Yeah, okay, it was pretty bad. Other than the Winchesters, Crowley likes to call us “Moose and Squirrel.” Dunno how that got started.

Sam: Don’t know how it started, but boy do I wish it would stop. Wasn’t Crowley also the one who really made the trend of others calling us “boys” get out of hand? It used to be just a Bobby thing, but then everyone started doing it.

Dean: Yeah, he was. [Grumbling] Which we’re not. We are grown-ass men, dammit.

**Notes for the Chapter:**

> Yes I borrowed Jared's terrible joke from that one panel because I feel like if it was Sam and Dean, the roles would have been reversed. I've wanted to use that idea for a long time now. >w<
> 
> (If for some reason you have no idea what I'm talking about, I implore to look at this bit: https://www.youtube.com/watch?v=q28sSS29QQ8)


	12. Question # 11: Whose room is a mess?

Sam: Actually, we both take pretty good care of our rooms.

Dean: Living in crap motel rooms your whole life kinda makes it hard to take having your own space for granted.

Sam: You’ve surprised me with how neat you’ve kept your room, I’ll give you that. But…

Dean: But?

Sam: I’m just saying…I’ve walked in there a few times and found empty beer bottles and unwashed dishes lying around.

[Dean looks ready to refute that, but reconsiders.]

Dean: …Yeah, alright, I have a habit of leaving plates and bottles in there. But I do a weekly clean-up to get rid of them eventually!

Sam: [Can’t help but be a bit smug] So I can claim the cleanest room in the bunker, then.

Dean: Yeah, keep that title all to yourself, you neat freak. [Playfully punches Sam’s arm]


	13. Question #12: What's your favorite game to play?

Dean: Not much time for fun and games in our line of work.

Sam: We hustle pool a lot, but honestly, that gets old. It’s a good way to make some quick money, but you can only knock balls around with gullible bar dwellers for so long before it gets tedious.

[Dean snorts. Sam gives him a look.]

Sam: What?

Dean: _Phrasing_ , Sammy.

Sam: [Realizing his accidental innuendo] Oh, c’mon dude.

Dean: Other than uh, “knocking balls around,” Sam loves a good game of rock paper scissors. Because he always wins, and it’s totally unfair.

Sam: Only because you always use scissors. You almost make it too easy most of the time.

Dean: [Getting distracted as he thinks to himself] Yeah…yeah, I do.

**Notes for the Chapter:**

> I probably didn't make it clear at all, but the way Dean trails off at the end there is a super loose reference to a post I saw a long time ago. It theorized that the reason Dean usually loses the rock-paper-scissors matches so often is because he does it on purpose to prevent Sam from facing the most dangerous parts of a hunt. And ya know...I can't help but think of that all the time because Dean is such a good protective older brother. TwT


	14. QUestion #13: What is your favorite food/drink?

Sam: Dean’s easy: pie and beer.

Dean: Love me some pie.

Sam: I already know you’re gonna say sal-

Dean: [Jumping to interrupt Sam so he can say it first] Salad. Salad and green…health…fiber shakes, or whatever. [Shudders at the thought] I wouldn’t be surprised if Lucifer himself came up with those unnatural leaf purees. Shakes are not meant to be green unless they’re mint chocolate chip flavor!

Sam: They’re really not that bad, Dean. It’s not so much for the taste; it’s supposed to be healthy for you.

Dean: [Grumbling to himself] Looks like Jolly Green Giant piss.

Sam: [Face scrunches up] …Thanks for that mental image, Dean. Thanks for that.

Dean: [Smirking proudly to himself] You are _most_ welcome!


	15. Question #14: What do you think about the most?

Sam: Not trying to call you out or anything, ‘cause you’ve been on pretty good behavior since we settled in the bunker, but you were a hell of a sex addict way back when. I swear it occupied, like, ninety-nine percent of your consciousness sometimes.

Dean: How is that not calling me out? That was life exclusively on the road, things were different back then! ‘Sides, I still get plenty of-

Sam: Aaaaand we’re stopping this conversation now before we get into TMI territory.

Dean: I bet ninety-nine percent of your consciousness is devoted to books and research. Gotta keep all that knowledge in your noggin somehow, eh Sammy?

Sam: Just out of curiosity, what do you think the other one percent is devoted to?

Dean: Um…hair care techniques. Yeah, that’s gotta be it.

[Sam just shakes his head, but he can’t hide a little laugh.]


	16. Question #15: Which sibling reads more?

[Dean slowly looks away from the camera and towards Sam. He dramatically extends his arms to gesture towards his brother.]

Sam: Yeah, I’m, uh, I’m the bookworm here.

Dean: Every time we have a day off, he spends at least half of it in the library. He’s got to have read every book in the entire bunker several times over at this point.

Sam: I dunno about _that_ …

Dean: My eyes get tired just _watching_ him read. I don’t know how he does it for so long…must be a college kid thing. He’s got eyes of steel.

Sam: Late nights studying the in the campus library will do that to you.

Dean: And he’s always been like this, even when he was a kid! Couldn’t go a day without burying his nose in some book he managed to get his hands on. _He even made his own friggin’ reading list._ Once a nerd, always a nerd.

Sam: …Am I supposed to be taking this as praise, or…?

Dean: Take it as whatever you want. [Grins] You nerd.


	17. Question #16: What is something you'd love to do together?

Dean: You know what? Two words: Beach. Vacation.

Sam: A beach vacation? Where’d that come from?

Dean: I’ve just been thinkin’, after something Cas mentioned in the video we did together. Wouldn’t it be nice to just…get away from it all for a while, go to a beach or island somewhere? Cas would come along, and we could invite Charlie and Kevin too.

Sam: …That sounds really nice, actually. It’s been years since a case has taken us near a beach, hasn’t it?

Dean: I haven’t even seen proper, fresh white sand since we were teens. It was a case with dad hunting a…what was it, again?

Sam: A siren, wasn’t it?

Dean: [Snaps his fingers] Yeah, right! Damn thing nearly got him, too, when it… [He freezes up and trails off]

Sam: What? When it what?

Dean: It, uh… [Sighs] Made itself look like mom. Picked dad’s brain pretty damn well.

Sam: [Surprised] Oh…I don’t remember that. Don’t remember much about that hunt at all, actually.

Dean: Not surprising. You were down for the count with a nasty head cold. Which was a real shame, ‘cause you barely got to enjoy the beach.

Sam: …Yeah, the more I think about it, we really are due for a vacation. The next time things go quiet on the supernatural front, we’ll pack up and take everyone to the coast.

Dean: [Grumbling to himself] No telling when that’ll happen. But, I’ll look forward to it. I kinda owe you anyways; back on that hunt, I promised I’d treat you to beach ice cream. [Smiling to himself] Nothing beats beach ice cream.


	18. Question # 17: Who is the most talented between you?

Dean: [Raising and eyebrow and leaning towards the camera] Is this a competition? Because that can be arranged.

Sam: It’s kind of an open-ended question. Depends on what you’d define as “talented” since we’re both good at different things.

Dean: How about something we both do, then? Like hunting.

Sam: Well…in that case, you’ve got me beat.

Dean: [Frowning] Uh, no, I was gonna say you had me beat. You’ve got all the tact when you hunt, you’re usually good at being careful.

Sam: And you’re better at just going in and doing things quick and efficiently. It’s like we balance each other out, actually.

Dean: Must be why we’re such a good team!

Sam: So we call it a fair tie for now?

Dean: Sure. [Smirks] Unless you’re up for that competition, because that can still be arranged.

Sam: [Unamused] …No.


	19. Question #18: What's your favorite makeup brand?

[Both brothers stare at the question in confusion.]

Dean: …The hell is this doing in here?

Sam: For sisters, I guess?

Dean: Guess this one doesn’t apply to us, then. [Grinning to himself as he gets an idea] Er, doesn’t apply to me. You on the other hand, Samantha…

Sam: [Dons bitchface] Dude. Really?

Dean: Yeah! [Holds up hands disarmingly] I mean hey, I don’t judge, I’m just sayin’ if you need to get in touch with your feminine side-

Sam: You are projecting so hard right now it’s not even funny.

Dean: [Freezing up] I’m, uh, not-

Sam: And makeup isn’t only a feminine thing, either. There’s stage makeup and face paint too- and hell, we’ve even used concealer to hide injuries when we’re on cases before-

Dean: [Resigned] Yeah, okay, I get it. We’re skipping this one. [Quietly to himself] I don’t even know any makeup brands.


	20. Question # 19: What is your sibling really bad at?

Sam: Hmm… [Thinks for a few moments] Well, Dean’s what we call emotionally-constipated.

Dean: [Taking slight offense at that] But I’m getting better!

Sam: Yeah, he’s getting better. He’s at least a hell of a lot better than he used to be. But for all the things he _can_ talk about, feelings do not come naturally. [Going quieter but still making sure Dean can hear him] Which is probably a big reason why that crush of his is still just a crush.

Dean: [Going a little red but outright ignoring that last bit] And Sammy’s got…talkin’ about feelings or whatever down pat, but how many times have you accidentally mistaken civilians for monsters and had to deal with the awkward aftermath?

Sam: [A bit defensive] Oh, like you haven’t done that too.

Dean: Just a few times, nowhere near as many as you. It’s hard enough to keep a low profile when you’re so tall and stand out like a tree everywhere we go-

Sam: Height has advantages too, you know.

Dean: …True. For example, you’re so tall that if we put a radar on your head, we’d have like, perfect internet wherever we went. You’d be our personal wi-fi hotspot. [Pauses to consider something] Then again, you already seem to have wi-fi all the time…are you _actually_ a walking wi-fi tower? Did I just uncover a conspiracy? I bet you’re hiding the antenna in all that hair! [Reaches to ruffle through Sam’s hair]

Sam: [Batting Dean way] Hey, hey! I just got through fixing this.

Dean: [Relenting, laughing to himself] Back to the point, Sam here is on the clumsy side sometimes. Can’t really help it, moose aren’t exactly known for gracefulness.

Sam: …I am seriously gonna kill Crowley one of these days for coming up with that nickname.


	21. Question #20: What is your sibling really good at?

Dean: Sam’s got a talent when it comes to technology; more specifically, troubleshooting technology. Computer not working? Sam’s got it. Netflix won’t load? He’s there. Wi-fi router that may or may not be hidden in his hair acting up? He’s your guy.

Sam: [Shrugs] I dunno why, but technology seems to listen to me most of the time. I think that’s actually why I have wi-fi all the time, by the way.

Dean: Technology always obeys to you. I dunno how you do it, but technology is your bitch!

Sam: Or maybe it just seems like that in comparison, because you… [Shakes his head a little] There’ve been times when you don’t seem to be technologically literate at all.

Dean: At least I’m better than Cas.

Sam: [Grimacing] Oof, you’re right. If I thought having to show you the wonders of task manager was a pain, that was nothing compared to having to teach Cas about how to use _every single function on a computer from scratch_. You know, it’s kind of exhausting being the go-to troubleshooter for you guys. Thank god Charlie’s here now, she can help too…

Charlie: [Chiming in from another room] You’re welcome!

[Both Winchesters are a little startled by her addition, but recover quickly and refocus on the question.]

Sam: But even though you’re always finding new ways to mess up my laptop, you _are_ really good at mechanical things. The way you take care of the Impala is…well, it always impressed me. And you made an EMF reader from a Walkman, which still kinda blows my mind.

Dean: Cars are easy! They don’t freeze to load in the middle of a Game of Thrones episode or pop up with a blue screen of death at the worst possible time. They’re nice and predictable…most of the time. [He stares into space for a moment, a devious smile creeping onto his face as he turns to Sam] Hey Sam, what do computers and cars have in common?

Sam: [Preparing himself for a horrible punchline] …What.

Dean: When something goes wrong with ‘em, they crash.

[Charlie snorts from the other room. Sam shakes his head in disapproval but is fighting a grin off his face.]

Sam: I take it back, _that_ was the worst joke you’ve ever made.

Dean: Shut up, I’m hilarious!

**Notes for the Chapter:**

> I came up with that terrible joke on my own, so if you wish to direct your wrath towards it at someone, take aim at me. After I made that connection, I couldn't stop thinking, "You know who would make a bad joke like this? Dean."


	22. Question #21: What is the best thing about each of you?

[Dean leans forward, puts his elbow on the table and rests his head in his palm. He raises his eyebrows and smirks at the camera.]

Dean: I’d like to think it’s my stunning charisma and good looks.

Sam: …Oh, so now we’re answering for ourselves, are we?

Dean: [Falling back into his chair] I dunno. What do you think is my best quality?

Sam: [Seriously thinking about it] Probably…your perseverance? Even when you’re backed into a corner or you want to give up, you don’t. And you’ve been in some _tough_ situations that would’ve broken most people a long time before you. Honestly, that inspires me to keep carrying on, too…I guess instead of perseverance, you could also call it stubbornness, but whatever it is, it works.

Dean: Stubbornness. [Snorts] I got that, alright. You’ve persevered through a lot of tough stuff too, but for your best quality I was thinkin’ more along the lines of empathy. Maybe I’m just extra grateful for that ever since you lost your soul, but you really are good at the touchy-feely stuff. And _that_ inspires me to work at getting better with… [Squints as he thinks of how to phrase it] Feelings…talk…or whatever.

Sam: So we still make a good team?

Dean: Damn right we do! Winchesters forever! ‘Cause…no matter the universe’s best efforts to get rid of us, we just can’t seem to stay dead, heh.


	23. Question #22: Who takes longer to get ready in the morning?

Dean: [Immediately and energetically points to his brother] Him! Definitely him! It’s that friggin’ _hair!_

Sam: The downside to long hair is the high maintenance, I’ll give you that. Still worth it, though.

Dean: Yeah, for me it just takes one quick “fwip” [Swipes his hand through his hair] and it’s done. When we’re staying in a motel, I can hear him brushing that monstrosity for five whole minutes, and it’s always when I’m waiting on him to hit the road.

Sam: I could make it take a lot longer than that; when I’m here at home, I let myself draw it out for a few extra minutes. I just take your impatience into account when we’re out because I’m such a good brother.

Dean: Still…you could save a hell of a lot of time if you’d just let me take some scissors and-

Sam: _No._


	24. Question #23: Which of you is closest to your parents?

[There’s a bit of an awkward silence. Both of them look at the question and deflate a little. It takes more effort than it should for them to look back up at the camera.]

Dean: Yeah, ‘bout that…

Sam: We, uh…both our parents are dead. Our mom was killed by a demon when we were really young. I didn’t even know her, but Dean… [Glances at his brother] …I’ll just let him do the talking.

Dean: Yeah, our mom- Mary Winchester -awesome lady. Used to be a hunter, settled down with our dad and tried to live a normal life. But we all know how _that_ ends up going ninety-nine percent of the time; case in point, friggin’ _Yellow-Eyes_. Still, she was the best when she was around. Made the greatest apple pies in the whole damn universe, had the perfect singing voice… [Is actually getting ever-so-slightly teary-eyed, but he blinks a few times to get himself under control] I wish you could’ve known her, Sammy, I really do.

Sam: Uh, well I did get to meet her once, technically. [Looks at the camera and realizes he has to clarify] Time-travelling shenanigans. An angel travelled back in time to try to kill our parents so we could never be born, long story.

Dean: Right. And as for dad…well, he’s just dad.

Sam: He was the one who got us into the hunting life. Trained us well, but…I never really got along with him as well as I should’ve.

Dean: So…wow, I never really thought about it, but I was closer to both of our parents than you ever were. How did you deal?

Sam: Honestly? I had you.

Dean: [Laughing to deflect the feels] Oh, shut up you big girl.

Sam: I’m serious! You were like a brother, mother, and father all at the same time. Dad was hardly around, mom was gone, and that just left you. You did pretty good with what you had, but I can’t imagine it was easy on you.

Dean: Nah…I just had to make peanut butter and banana sandwiches for you on the daily, you dietary freak.

Sam: Okay but have you ever actually tried one? They sound weird, I know, but they’re surprisingly good! [Turning more serious again] But no, really, I know it wasn’t easy on you to have all that responsibility. I owe you a lot for all that.

Dean: [Not entirely sure how to respond] No big deal…I was doin’ my job. And I still am; you’re _still_ a handful sometimes. But I musta done something right, ‘cause you turned out to be a good kid.

Sam: I’m still thirty-three, Dean.

Dean: And I still have seniority!


	25. Question #24: Who’s hot? ;)

Dean: …I don’t appreciate the insinuations of this question.

Sam: What?

Dean: Ya know, you say one little thing wrong, and those people- what’re they called, shippers? -will leap on it like starving lions. All it takes is one misplaced winky face. You know fully well that there are people out there who don’t care that we’re brothers-

Sam: [Chuckling to himself] Dean, I don’t think anyone is going to-

Dean: Let’s just say this: it’s not exactly a secret that us Winchesters are known for being attractive. We’ll leave it at that and call it a fair tie. [Quietly to himself] Unless we’re judging by how many chicks one of us can pick up in one night, in which case I win outright.

Sam: What? That is totally unfair criteria. Maybe that’s how you go about it, but that’s not exactly my style.

Dean: Ahhh right, you gotta wine and dine ‘em first. Mr. Classy Almost-College-Graduate is above those common tactics. Or maybe…people are scared off by that massive mane you pass off as a hairdo.

Sam: For your information, some people actually like long hair on a guy. Which you should know, considering you watch Dr. Sexy religiously and sing the praises of his luscious locks every friggin’ episode.

Dean: [Face goes red] That’s completely different! Bad example! Dr. Sexy transcends all laws of attractiveness and you know it!

Sam: …I think we need an impartial party to decide this for us.

Dean: You’re right. Call in the lesbian.

Sam: [Cupping a hand around his mouth and shouting off-screen] Hey, Charlie! Which of us is more attractive, me or Dean?

Charlie: [Voice echoing in from a neighboring room] Um, why are you asking me? I’m not exactly the expert on what makes a guy hot.

Dean: Just answer the question, Charlie. It’s for…posterity, or somethin’. I honestly don’t even know at this point.

Charlie: [Takes a moment to reply] Well, from what I’ve seen among the community of Supernatural fans, a lot of people think both of you are smokin’. Fans literally get into all-out wars on the subject. So…suffice to say, you’re both in high demand.

Dean: …Wow. I never thought my looks would literally inspire a war. Kinda humbling, in all honesty.

Sam: [Shaking his head] Let’s just call this a tie and move on.

**Notes for the Chapter:**

> I did _not_ put that winky face there. The website I got these questions from put it there, and I left it because I thought it was funny.  >w<


	26. Question #25: What’s one thing you can do that your sibling can’t?

Sam: Um…I can do this. [Shakes his head around to send his hair flowing gloriously through the air]

Dean: [Crosses his arms and watches the display with an unimpressed frown] Forgive me for not being jealous of your lady-hair physics.

Sam: [Smiles sweetly at the camera] Aww, he is jealous.

Dean: Am not. ‘Sides, I’ve still got you beat in one area for sure: dancing.

Sam: I’ll admit, you are a really good dancer, but I’m not _that_ bad-

Dean: Junior prom. Knoxville High. Eleventh grade.

Sam: [Eyes going wide with fear] Oh no, you are _not_ telling that story here-

Dean: We were only in town for, what, a week? Dad stopped there for a hunt nearby, just happened to drop in around prom season. Sam actually managed to get himself a date- what was her name, Bailey? We’ll go with that. Anyway, I should’ve done the responsible thing and told him what all to expect at the prom scene, but I had this date of my own ya see, and I was a little busy trying to figure that out-

Sam: [Resigned to the fact that this story will be told] Just get to the worst part.

Dean: Right, so he and Bailey are off to the side making awkward small talk about…books, or somethin’. She had to have been a nerd if you were her type. But then, of all the songs that could’ve possibly come on, Footloose started playing. Bailey drags him right into the middle of a crowd of other kids, and they start dancin’ and…well, let’s just say Sammy’s feet really were loose; way too loose.

[Sam groans and hides his face.]

Dean: Then… [Snickers] Somewhere in the middle of that, those loose feet of his step on the end of Bailey’s long purple dress, and I dunno if it was just a little big on her, or if she didn’t fasten it right or if Sam’s dance moves really were that uncoordinated, but it came tumbling down around her like a detonated building. Poor girl was _mortified_ , but nowhere near as mortified as Sam. She ran off to the bathroom in her underwear and wasn’t seen for the rest of the night. Wherever she is now, I hope she’s moved on to bigger, better things. [Laughs to himself for a few moments] But the thing that always gets me is this: you just _know_ that she uses the whole thing as a funny anecdote to share at parties now!

[Dean openly laughs some more. Sam finally uncovers his face, which is quite red.]

Sam: Years. It’s been years and you still haven’t let that go.

Dean: He hates Footloose now, too! Can’t stand it! I’m gonna have to remember to play it next time we’re on a drive somewhere.


	27. Question #26: What’s a weird habit your sibling has?

Dean: Okay, I really wasn’t planning on bringing this up, but now’s as good a time as any…Sam, what’s with the curlers?

Sam: [Eyes dart towards Dean] The…what?

Dean: The curlers! The ones I found in your bathroom cabinet?

Sam: [Getting peeved] What were you doing snooping around my cabinet?

Dean: [Holding up his hands disarmingly] I was just looking for some painkillers to deal with a migraine! I wasn’t tryin’ to dig up any of your embarrassing hair care secrets.

Sam: …Okay listen, I was serious when I said my hair is high maintenance-

Dean: [Bursting with laugher on each word] Oh my _god_ -

Sam: Charlie suggested it, okay? They really do work, I wish I’d had them a long time ago. [Holds a finger up in Dean’s face] And before you can say another _word_ , no, curlers aren’t just for women, because I know you’re gonna try and distort it through some lens of overcompensating hypermasculinity like you always do.

Dean: [Still chuckling] Chill, Sam, I’m not judging you. If they work, they work, intended female demographic or not. But, uh… [Can’t help it, he snorts] You…you thinkin’ about putting some glitter or hot pink hair dye in there or somethin’ too?

[Dean is shaking and stifling laughs with his fist. Sam is, as usual, utterly done.]

Sam: [Frustrated] You know what? You wanna be like that, fine. I _definitely_ wasn’t planning on bringing this up ever, but I guess now really is as good a time as any, huh? Dean, I’ve seen them.

Dean: [Still brimming with laughter] Seen what, my magazine stash? I’m not exactly tryin’ to hide those.

Sam: No, listen. The… [Catches the camera out of the corner of his eye and spares a thought for Dean’s privacy] Um…pink. Satin. I…think they had lace on them?

Dean: [Confused but very amused] The hell are you talking abou- [His face falls and he immediately turns extremely pale] N…no, you didn’t-

Sam: [Casually crossing his arms] Oh, I did. I saw something pink sticking out of your duffel on a hunt a while back, and of course I had to see what it was. Don’t know what I expected, but…it certainly wasn’t that.

Dean: [Scrambling for an excuse] No, listen, those aren’t-

Sam: And I dunno if you’ve gotten really sloppy at packing your clothes, but I’ve caught glimpses of them in your bag multiple times on multiple trips at this point. I don’t have a clue whether you just carry them around for some reason or actually wear them, I don’t really care-

Dean: [Getting mortified] _Why_ is this my life-

Sam: But, whatever the case, safe to say it’s a habit that falls outside the norm. [Holds up a hand] Not that I’m judging you!

Dean: [Burying his face in his hands for a moment] Just…shut up.

Sam: I’m serious, I’m not! I’d rather not have ever seen them, but I can’t undo that now, so…I’m just saying, maybe you should try to be a bit more discreet about keeping them out of sight if that’s what you want.

Dean: [Finally looks up, points a very stern finger at Sam] Not a soul. You do not tell a _soul_ , understand?

Sam: Wasn’t planning on it.

Dean: Okay. Now we never, ever speak of this again, _ever_.


	28. Question #27: Who is sensitive?

Sam: If we’re judging by how that last question went, I’d say it’s Dean-

Dean: _Not speaking of that!_

Sam: …Okay, fine. He doesn’t show it, but man does Dean have some crazy emotions bottled up in there.

Dean: Yeah, right back atcha. But having hellish, traumatic lifetime experiences doesn’t necessarily make someone sensitive. If anything, I’d think it’d make them way tougher.

Sam: That’s fair. If you’re a hunter for any extended period of time, you get desensitized more than anything.

Dean: [Addressing the camera] Which actually brings to mind an important Winchester PSA: don’t be a hunter if you can avoid it. More and more I hear about people romanticizing it, but take it from us, it sucks. Sure, you get to save people and destroy evil, but the cost is more than most people realize.

Sam: Like, for example, dying. Er, multiple times, in cases like ours… [Side-eyes the camera] Actually, if anyone’s watching this, chances are they’re already involved in the supernatural somehow, so it may be a moot point. But, if for some reason you’re watching this and you’re not a hunter, don’t aspire to be one.

Dean: All that being said, I’m casting my vote for Sam being the sensitive one. He thrives on chick flick moments.

Sam: …You do remember that _you’re_ the one who cried at The Lion King, right?

Dean: I did not!

Sam: You think you may have hidden it, but I saw you wiping tears away.

Dean: [Quietly] Mufasa was worthy of a few tears. You can’t tell me you weren’t crying internally when Simba found him.

Sam: [Shrugs] I mean, yeah, it was sad, but…they’re cartoon lions, Dean.

Dean: Cartoon lions who deserved better! Lion King’s an unfair comparison anyways. I’ve seen your heartstrings get tugged on by way less out there in the real world.

Sam: Let’s just settle for this: if you’re looking for open sensitivity, I win, but if you’re looking for internalized sensitivity, Dean wins. Fair?

Dean: [Sighs] …Fair.


	29. Question #28: Describe the last thing you did with your sibling.

Dean: Ooh! [Rubs hands together] We actually just got back from a hunt a couple states over this morning. We were dealin’ with a soul eater- tricky bastards, all of ‘em -and Sam nearly got stuck in its pocket-dimension-nest-whatever.

Sam: [A smile momentarily twitches onto his face and he looks at the camera] That’s a highly technical hunting term, for those of you who don’t know.

Dean: Shut up, you know what I meant. Anyways, I saved his ass with a sigil and it was all fine. There is nothing more satisfying than watching one of those things shrivel up and be sent off to Purgatory. Justice served for all those souls it trapped over the years.

Sam: That one had a lot of souls in its nest, I’m glad we cold free some of them. We’d been on the road for a while before that, too. It’s just been one hunt after another lately…

Dean: Yeah, that soul eater was just a pit stop in a series of other baddies. Originally we’d gone out chasing reports of witch activity in Virginia-

Sam: [Snapping his finger as he remembers] Wait, wait, first we had to stop in Kentucky ‘cause we just happened to find a quick Revenant case in one of the towns we passed through.

Dean: [Nodding] Yeah, I nearly forgot. That was pretty much an in-and-out kinda case, we had time for it even with insane witches casting spells to make people into their own personal house slaves next door.

Sam: And the demon, don’t forget the demon.

Dean: [Suddenly angry] Yeah, that- damn- [Gets ahold of himself so he can explain] They were borrower witches, amateurs in way over their heads. Really needed the demon mojo to power their sadistic mind-control magic. Friggin’…witches.

Sam: The demon really did not wanna give up the antidote for those spells, either. Would’ve been so much easier to kill it outright like we usually do, but…when push comes to shove…

Dean: That’s when you bring out the torture. That demon did _not_ know what hit it.

Sam: [Half smiles] Yeah, word to the wise: don’t get on the wrong side of a Winchester if you’re a monster. It doesn’t end pretty for anyone.

Dean: Then we ganked the demon, ganked the witches, and freed the people with enough time leftover to stop for celebratory pie at the local diner!

Sam: _You_ stopped for celebratory pie. I stayed in the car and found us the soul eater case.

Dean: Because monsters never rest and we can never catch a freaking break. But once _that_ day was done and we’d stopped for _another_ celebratory pie slice, we finally made it back home to our housemates.

Sam: Which consist of a fallen angel, an energy drink-chugging prophet, and a genius computer hacker who recently got back from her vacation to Oz.

Dean: …What even are our lives?

Sam: That… [Sighs] is a really good question.

Dean: I mean, think about it. Most siblings who decide to go through this list, for whatever reason, probably answer this question with something like, “we went grocery shopping,” or “oh yeah, just took a friendly walk around the ol’ neighborhood to say hello to all the other picket fence dwellers!” I bet no one has ever had an answer that involved demon torture.

Sam: At least it’s never dull.


	30. Question #29: Complete this statement: my sibling is…

Dean: [Grins] A big ol’ nerd, kind of a bitch, a hunter with a good heart, and if Crowley’s to be believed, a moose.

Sam: [Raises an eyebrow] Good heart, huh?

Dean: What? It’s true! [Crosses his arms and looks up] Just thought I’d end the video on a good note is all.

Sam: [Smiling despite himself] ‘Kay then, my brother is…an overly-confident flirt, kind of a jerk, a skilled hunter who, no matter how much he may deny it, _also has a good heart_ , and if Crowley really is to be believed, a squirrel.

Dean: [Chuckling humorlessly] C’mon now, Sam, you’re the one with the-

Sam: [Determined not to let him finish] No, you said you wanted to end this video on a good note. You may have a different kind of good heart, but it is still definitely a good heart, okay? And everyone looks up to that. I know I do, I know Cas does, and so do Charlie and Kevin.

Dean: …I dunno when this turned into Hallmark heart-to-heart territory, but I’m stopping it now.

Sam: [Smirking triumphantly] That a high enough note for you to end on?

Dean: Fine, whatever. We’ll call this done. [Pauses] You uh, wanna call the bunker together for that Star Wars marathon?

Sam: [Scoots his chair back and stands up] You make the popcorn.

Dean: [Rolls his eyes good-naturedly and reaches towards the camera] Fine, bitch.

Sam: [Now offscreen] Jerk.

[Something clicks as Dean haphazardly fiddles with the camera. The frame shakes a little and cuts to black as the video ends.]

**Notes for the Chapter:**

> Nooooo it's the end ;w; I had a lot of fun with this installment, and if you're looking for more, fear not! I have more of these planned for the future.
> 
> In the meantime, I'm currently working on patching up another fic that's been a year in the making so I can post it here. It's gonna be the longest and silliest one I've uploaded yet, so hold onto your hats folks OwO


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